Triphenylphosphine → HCID 90418267, compound

HRID 2177310Notes

Reaction equation

[Br:1][C:2]1[S:6][N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[C:3]=1[CH2:11][OH:12].[F:13][C:14]1[CH:15]=[C:16]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:17]=[C:18]([F:21])[C:19]=1O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Br:1][C:2]1[S:6][N:5]=[C:4]([C:7]([F:9])([F:10])[F:8])[C:3]=1[CH2:11][O:12][C:19]1[C:18]([F:21])=[CH:17][C:16]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15][C:14]=1[F:13]

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed [5-bromo-3-(trifluoromethyl)-1,2-thiazol-4-yl]methanol (200 mg, 0.76 mmol, 1.00 equiv), methyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (199 mg, 0.92 mmol, 1.20 equiv), PPh3 (401 mg, 1.53 mmol, 2.00 equiv), tetrahydrofuran (3 mL), DIAD (3.9 mg, 0.02 mmol, 2.00 equiv). The resulting solution was stirred overnight at 25° C. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:4). The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 190 mg (51%) of methyl 3-(4-[[5-bromo-3-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate as yellow oil.

Workup

customInto a 25-mL round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 190 mg (51%) of methyl 3-(4-[[5-bromo-3-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate as yellow oil

Sources & evidence

ORD record: ord-b5a1bd16c7204c8fa2169ab29ed733bf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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